Is there a % probability of success that you can retry for another chance or is there a threshold you must overcome before you can succeed at all? I keep increasing my pickpocket and stealth skills but haven't even been able to take one ruble from a peasant, so I'm wondering.

On a related note: is there a manual I can download that explains this and other mechanics? I don't see anything of the sort between the game's files, and it's a little too new to find anything on GameFAQs.

I second this.

In depth PROVEN details about pickpocket / stealth mechanics are badly needed as a pinned topic.
From what i have been able to gauge (i could be completely wrong btw) there are a few things you have to take into account.

Npcs being near by.
The quantity on the item you are trying to steal.
The quality of the item. (decent guns are almost impossible to steal early game).

I am fairly certain these things apply, however i still cant say for sure because of the weird ass RNG.

::Questions id like to add also :)::

At what distance do npcs begin to effect pickpocket / stealth?

Does stealth effect pickpocket at all, or is it just for stealing stuff from houses, safes, etc?

Do npcs need to face you in order for them to effect pickpocket / stealth?

Do you have to be directly behind the target to effectively pickpocket?

Why the F do i fail so often with 135 pickpocket and 128 stealth, pick pocketing garbage items, on guards / merchants? lol

Are gun vendors in cities impossible to pickpocket, if not what skill levels would you need?

Are certain guards in the city impossible to pickpocket?

Does stealth allow you to pickpocket more effectively, if so, in what way?

Does pick poketing at night increase your chance of success / effect stealth?

When your caught pick pocketing and see the message"pick pocketing failed youve been cought red handed", is that the games way of telling you your stealth is crap and you were seen, or is it that pickpocket skill is too low?

Someone please explain these mechanics (pickpocket / stealth) in depth.

Would be awesome if the Dev could chime in on this one.